Thermoset monomers are used to make commercially useful articles. They are also used in a variety of adhesive compositions. Monomers used in these applications include acrylate, methacrylate, fumarate, maleate, maleimide, and stryenic functional compounds. Resistance to hydrolytic degradation of the adhesive bonds formed from these thermoset adhesives is often a critical performance requirement. The performance of these adhesives, in the presence of hot and wet environments, is directly connected to the hydrolytic resistance of the chemical linkages within the monomers themselves.
There remains a need to produce hydrolytically stable, free radically polymerizable monomers to meet the increasing demands of the electronics and other industries.
It is well known in the art, that the esters of secondary alcohols are significantly more resistant to hydrolysis than esters of primary alcohols. Nevertheless, few radically polymerizable thermoset monomers containing these desirable secondary alcohol ester linkages have been developed despite a clear need for such compounds and their potential widespread application. The only readily available monomers in this class include isobornyl acrylate, isobornyl methacrylate, 3,3,5-trimethylcyclohexyl methacrylate, and cyclohexyl methacrylate. Thus, although such alcohols have the potential for filling the need for hydrolytic stability, the paucity of monomers having the above-mentioned characteristics limits their current potential in the adhesives and other industries.
There remains a need to produce hydrolytically stable, free radically polymerizable monomers to meet the increasing demands of the electronics and other industries.